Abstract
The structure of a glyoxalase I inhibitor (I), isolated from a cultured broth of Streptomyces griseosporeus, was found to be 2-crotonyloxymethyl-4,5,6-trihydroxy-cyclohex-2-enone by chemical studies. Stereochemistry and absolute configuration were determined to be 4R, 5R and 6R by X-ray crystallographic analysis of a bromine-containing crystalline derivative. The crotonyloxy group of I shows a surprising proclivity to be displaced by SH-compounds. This property is shown to be the basis for its biological activity.
MeSH terms
-
Antibiotics, Antineoplastic* / isolation & purification
-
Antibiotics, Antineoplastic* / pharmacology
-
Butyrates*
-
Chemical Phenomena
-
Chemistry
-
Crotonates* / isolation & purification
-
Glutathione
-
Lactoylglutathione Lyase / antagonists & inhibitors*
-
Lyases / antagonists & inhibitors*
-
Mercaptoethanol
-
Streptomyces / analysis
-
Structure-Activity Relationship
-
Sulfhydryl Compounds*
-
X-Ray Diffraction
Substances
-
Antibiotics, Antineoplastic
-
Butyrates
-
Crotonates
-
Sulfhydryl Compounds
-
Mercaptoethanol
-
Lyases
-
Lactoylglutathione Lyase
-
Glutathione